US2779782A - Method of manufacturing dimethyl terephthalate from xylene dichloride - Google Patents
Method of manufacturing dimethyl terephthalate from xylene dichloride Download PDFInfo
- Publication number
- US2779782A US2779782A US447387A US44738754A US2779782A US 2779782 A US2779782 A US 2779782A US 447387 A US447387 A US 447387A US 44738754 A US44738754 A US 44738754A US 2779782 A US2779782 A US 2779782A
- Authority
- US
- United States
- Prior art keywords
- grams
- acid
- dimethyl terephthalate
- mixture
- reaction mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 title description 2
- 239000008096 xylene Substances 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 22
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims description 7
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052572 stoneware Inorganic materials 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- -1 p-chloromethyl benzoic acid ester Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
Definitions
- This invention relates to the manufacture of the dimethyl ester of terephthalic acid. More particularly it is directed to the manufacture of said ester from pxylylene dichloride (u,u-dichloro)-p-xylene.
- the dimethyl ester of terephthalic acid is obtained in the yield of Example 2 350 grams (2 mols) of p-xylylene dichloride, 800 grams of HNOs (65%) and 300 grams of water are heated for about 5 to 6 hours to a temperature of about C. while being vigorously stirred. Then phosphoric acid is added to the reaction mixture while gaseous hydrogen chloride is simultaneously introduced. 2000 grams of methanol are added to the reaction mixture dropwise. The mixture is further heated for about 8 to 10 hours at a temperature of about 100 C. Upon cooling the dimethyl ester of terephthalic acid separates out in solid form, the deposited product containing a small amount, for example, of terephthalic aldehyde acid ester. Upon recrystallization of the product, using methanol for example as the recrystallizing solvent, the dimethyl terephthalate is obtained in pure form having a melting point of 141 C.
- reaction is carried out by passing a stream of gaseous hydrogen chloride through the reaction mixture, and in the presence of a member of the group consisting of phos 4 h r a d lsivin s ium bi ha nhatsa 1292a? Bg g en e rC wdin 11. fil: of this p tq 'sfu m bifilibphia te, and calciflm biphosphate. v UNITED STATES PATENTS 5.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE326540X | 1953-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2779782A true US2779782A (en) | 1957-01-29 |
Family
ID=6184041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US447387A Expired - Lifetime US2779782A (en) | 1953-08-03 | 1954-08-02 | Method of manufacturing dimethyl terephthalate from xylene dichloride |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2779782A (is") |
| BE (1) | BE530181A (is") |
| CH (1) | CH326540A (is") |
| FR (1) | FR1104720A (is") |
| GB (1) | GB761820A (is") |
| NL (1) | NL82225C (is") |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037048A (en) * | 1959-01-14 | 1962-05-29 | Glanzstoff Ag | Process for the purification of crude dimethyl terephthalate |
| US3060222A (en) * | 1958-12-23 | 1962-10-23 | Basf Ag | Production of dialkyl esters of iso-and/or terephthalic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610211A (en) * | 1947-10-04 | 1952-09-09 | California Research Corp | Preparation of aryl monocarboxylic acids |
-
0
- BE BE530181D patent/BE530181A/xx unknown
- NL NL82225D patent/NL82225C/xx active
-
1954
- 1954-07-19 FR FR1104720D patent/FR1104720A/fr not_active Expired
- 1954-07-21 GB GB21321/54A patent/GB761820A/en not_active Expired
- 1954-07-26 CH CH326540D patent/CH326540A/de unknown
- 1954-08-02 US US447387A patent/US2779782A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610211A (en) * | 1947-10-04 | 1952-09-09 | California Research Corp | Preparation of aryl monocarboxylic acids |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060222A (en) * | 1958-12-23 | 1962-10-23 | Basf Ag | Production of dialkyl esters of iso-and/or terephthalic acid |
| US3037048A (en) * | 1959-01-14 | 1962-05-29 | Glanzstoff Ag | Process for the purification of crude dimethyl terephthalate |
Also Published As
| Publication number | Publication date |
|---|---|
| CH326540A (de) | 1957-12-31 |
| FR1104720A (fr) | 1955-11-23 |
| NL82225C (is") | |
| BE530181A (is") | |
| GB761820A (en) | 1956-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3091632A (en) | Process for the production of glycol monoesters from aldehydes | |
| US8686181B2 (en) | Method for producing ethylene glycol dimethacrylate | |
| SU1041029A3 (ru) | Способ получени терефталевой кислоты | |
| US3264346A (en) | Process for the production of aqueous solutions of pure lower aliphatic percarboxylic acids | |
| JPS61172852A (ja) | 炭酸ジフエニルの製造方法 | |
| US3458561A (en) | Esterification of acrylic acid | |
| US4032563A (en) | Process for the recovery of high purity diesters of terephthalic or isophthalic acids | |
| US3264347A (en) | Process for making acrylic acid | |
| US2779782A (en) | Method of manufacturing dimethyl terephthalate from xylene dichloride | |
| US2879289A (en) | Oxidation of alkyl benzenes in the presence of alkanols | |
| US2838565A (en) | Purification of terephthalic acid | |
| US2858334A (en) | Preparation of phthalic acids | |
| US3705186A (en) | Process for the preparation of diphenyl terephthalate | |
| US2647141A (en) | Production of isophthalic acid | |
| US3816523A (en) | Process for the production and purification of benzoic acid | |
| US6235924B1 (en) | Continuous process for preparing benzoic acid esters | |
| US2513504A (en) | Esters | |
| US4014755A (en) | Method of refining pyromellitic acid dianhydride | |
| US3639451A (en) | Process for esterifying aromatic carboxylic acids | |
| US3014961A (en) | Process for the preparation of terephthalic acid and isophthalic acid | |
| US3013070A (en) | Process for the production of butane-1, 2, 4-tricarboxylic acid | |
| US2825737A (en) | Purification of dimethyl terephthalate | |
| US3235587A (en) | Process for the preparation of terephthalic acid having a high degree of purity | |
| SU734192A1 (ru) | Способ получени диметилтерефталата | |
| US3965168A (en) | 3-Carbamoyl-3-hydroxyglutaric acid and salts |